


Lipstick Kisses

by shipgrumps_equals_hashtag_boner



Series: Dress Ross Universe [2]
Category: Game Grumps
Genre: Blow Job, Lipstick, M/M, cross-dressing
Language: English
Status: Completed
Published: 2016-04-28
Updated: 2016-04-28
Packaged: 2018-06-05 03:44:31
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,545
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6687877
Author URL: https://archiveofourown.org/users/shipgrumps_equals_hashtag_boner/pseuds/shipgrumps_equals_hashtag_boner
Summary: <blockquote class="userstuff">
              <p>Ross tries out make-up for the first time.</p>
            </blockquote>





	Lipstick Kisses

It had been a few months since Brian had accidentally discovered Ross’s secret those months the pair had become much closer. Brian frequently visited Ross at his home and Ross quickly became more confident wearing his preferred attire around the older man, and Brian would encourage Ross to try new things.

Within a month of Brian finding out Ross had learnt how to walk in heels without almost breaking his neck although he still wasn’t one hundred percent comfortable in them and Brian could tell that upset him so he bought Ross a pair of black pumps to go with all of his dresses and skirts, as well as a pair of dark blue converse to go with his favourite dress. He wrapped the shoes in baby blue paper and Ross almost cried when he opened them, instantly attaching himself to the older man, kissing him.

“I love you,” Ross whispered, hoping the older man felt the same.

“I love you too beautiful,” Brian replied hugging the younger man back, wondering how someone could be so breathtaking.

In the second month they became boyfriends and didn’t keep that secret. Ross would go into the Grump space covered in hickeys and Brian would constantly flirt with his boyfriend in front of the others, loving how flustered Ross would get.

That month Ross decided to try out wearing panties, he always thought they looked cute, he often daydreamed about wearing them and how they would feel, and having Brian around was even more of a reason to try them out.

The night after Ross bought a pair of panties he teased Brian relentlessly, constantly dropping things and over-dramatically bending over, his black mini skirt riding up to reveal the baby pink panties.

It didn’t take long for Brian to realise what Ross was doing and the next time Ross bent over to pick something he had purposely dropped Brian moved himself to stand behind the younger man, his hands moving up Ross’s thighs pushing his skirt up.

“You teasing me baby girl?” Brian asked hands now on Ross’s ass, loving how soft the panties felt compared to boxers, admiring how they clung to Ross’s ass.

“Maybe,” Ross said playing coy as Brian massaged his cheeks through his panties.

“You look so cute like this baby,” Brian whispered, his hot breath hitting Ross’s neck that was already covered in hickeys from a few nights ago.

That night Ross came harder than he ever had before, ruining his new panties.

“I’ll buy you a new pair,” Brian muttered sleepily after they’d cleaned up.

By the third month Ross had accumulated many panties of different styles and colours. He had tried a bra, the smallest available, which was a training bra, but he found it uncomfortable, he also tried a bigger bra and stuffed it but he wasn’t into that either.

Ross wanted to try makeup, but looking at all the products overwhelmed him. He had no clue what would look good on him and he was too embarrassed to ask someone working there for help.

Brian noticed whenever they went out for a meal or shopping Ross’s eyes would wander to the make-up shops or aisles.

A few days past and Ross was busy recording so Brian bought some make-up for Ross, nothing too extravagant, just a light foundation, blue eyeshadow, back mascara and eyeliner, red lipstick and a clear lip liner, as well as some brushes. After buying the items he when to Ross’s home, Ross had already given him a key, showing how much he trusted the older man.

Ross was pleasantly surprised when he came home to see a small black bag on the table, he expected another pair of panties or something similar. Opening the bag, he couldn’t keep a smile from forming on his face when he saw the make-up. He called Brian straight away to thank him.

“You like my gift baby?” Brian asked as soon as he answered the phone.

“Fuck yeah, Brian. Thank you, everything looks so great, how did you know what to get?” Ross spoke in awe, whenever he looked he couldn’t choose anything yet Brian had somehow chosen everything perfectly.

Brian shrugged even though Ross couldn’t see.

“It’s like science, I do have a PhD. you know?”

“I know, I’ve seen it,” Ross giggled.

Brian sighed at Ross’s stupid joke, although he had a smile on his face.

“So how about you test the make-up out and I’ll be over soon,” Brian proposed seductively.

“Okay daddy,” Ross agreed voice filled with lust, before hanging up, eager to try the makeup out.

Ross set all the products out on the dresser in his bedroom but realised that he had no clue what he was doing. Which brushes were used for what? He guessed that foundation was applied first, but how much did he use? The eyeliner also scared him, what if he stabbed himself in the eye?

He heard a knock at the door and knew it was Brian, who expected him to be wearing some make-up.

Ross opened the door and Brian immediately saw the panicked look on Ross’s face.

“Hey Ross what’s wrong baby?” Brian questioned softly as he closed the door behind him. The last time he saw Ross like this was when he accidentally saw the younger man in a dress for the first thing.

“I was looking at the make-up and I have no idea what to do with any of it,” Ross explained, his eyes wide in desperation for help.

Brian led the younger man to the bedroom, looking at the makeup products before realising he also didn’t know what to do with them.

“Uh, we could try looking at some tutorials?” Brian suggested.

Firstly, they watched a few of Suzy’s tutorials but as amazing as they were they all seemed rather complex.

Eventually they found a simple tutorial and Brian began to apply the make-up to Ross’s face.

“Ross, I’m not going to hurt you, just stay still.”

They had finally gotten to the eyeliner and Ross had begun twitching, trying to distance himself from the eyeliner whenever Brian tried to put the pencil near his eye.

“Baby hold still or I will hurt you,” Brian almost threatened, his voice soft yet firm.

Ross tried to remain still as Brian applied the eyeliner. After he’d finished Brian sighed, it looked messy and uneven. He decided to smudge it, which made it look better, not great but it would do for now.

After that fiasco the lipstick was easy enough and Brian painted Ross’s lips a deep red colour.

“Okay baby girl, that should be it.”

Ross moved to stand in front of the mirror in his room, admiring the makeover Brian had given him.

He looked pretty, even though Brian always told him he was this was one of the first times Ross truly felt pretty or beautiful. His short black dress hugging his body, and the make-up bringing out his facial features.

Brian admired Ross, especially his now ruby red lips, he couldn’t help but imagine Ross’s lips leaving marks all over his body.

“You look so beautiful baby,” Brian said, packing the makeup away, clearing the bed, fairly confident about what would be happening soon.

“Like what you see daddy?” Ross teased, moving toward the bed, kissing his boyfriend’s lips, a trace of his lipstick left behind.

“Yeah baby girl,” Brian moaned as Ross unzipped his jeans, pulling them down.

“Daddy, you’re so hard,” Ross whispered slipping into his submissive role.

“What to help me out with that baby girl?”

Ross nodded eagerly, removing Brian’s boxers, his cock springing out, the head already shiny with precum.

Ross began kissing up Brian’s thighs, leaving lip shaped marks. Brian watched admiring the red marks Ross left behind.

Ross began to suck at the head off Brian’s cock, the salty taste that had become so familiar filling his mouth.

Brian’s hands met Ross’s hair, pulling Ross further onto his member, his ruby red lips stretched around his erection.

Ross was quick, sucking and licking Brian’s cock trying to get him off. One of his hands was touching Brian’s thigh, the other touching himself through his panties.

It didn’t take long for Brian to cum, shooting his load into Ross’s mouth. Ross sucked Brian dry, still touching himself.

“You gonna cum in your panties for me baby?” Brian’s said his voice husky.

“Yes daddy,” Ross moaned, the outline of his leaking erection prominent through his deep red panties.

Brian continued muttering sweet nothings until Ross cam hard, ruining yet another pair of panties.

The pair cleaned up, before cuddling in the bed. Brian wearing a t-shirt and boxers while Ross was only wearing a new pair of panties, light yellow panties that he didn’t really like but they came with a set.

“Hey Bri,” Ross whispered, head on his boyfriend’s chest.

“Yeah baby,” Brian asked, hugging his boyfriend tightly.

“I think I’m ready to tell the others.”

Brian smiled, kissing Ross’s forehead.

“Good, I’m proud of you, and although I know they’ll accept it, I’ll be by your side no matter what.”

Ross cuddled deeper into his boyfriend’s chest, wondering how he got so lucky.

“I love you.”

“I love you too baby girl.”


End file.
